


Pass/Fail

by PetrichorPerfume



Series: Rainbow Marbles [27]
Category: Supernatural
Genre: Blow Jobs, Butt Plugs, Comforting Dean, Crossdressing, Demon Dean Winchester, Incest, M/M, Orgasm Control, Orgasm Delay/Denial, Roleplay, Sexual Fantasy, Sexual Roleplay, Teacher/Student Roleplay, Teen Years, Vibrators
Language: English
Status: Completed
Published: 2014-06-28
Updated: 2014-06-28
Packaged: 2018-02-06 15:17:28
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,553
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1862598
Author URL: https://archiveofourown.org/users/PetrichorPerfume/pseuds/PetrichorPerfume
Summary: <blockquote class="userstuff">
              <p>Dean is trying to hook up with some random chick at the bar, or at least that’s what it said on the paper Dean had given them to read last night. Sam feels like it’s the punch line to a bad joke; the only people in the ‘bar’ are the three of them, because, surprise, the bunker came equipped with a 1920’s-style speak-easy, Cas is the ‘random girl,’ Dean is a demon, and Sam is pretending to be seventeen.</p>
            </blockquote>





	Pass/Fail

**Author's Note:**

> Based on this request by SamFan: More Dean-on-Sam action, please?! Maybe making him roleplay being a gangly teenager crushing on his older brother, either fulfilling fantasies Dean knows Sam had but never acted on or confusing or otherwise convincing Sam that he had harbored such fantasies (not sure whether Sam/Dean were a couple in this canon).
> 
> Warnings: Very brief mention of underage in the fourth and fifth paragraphs (if you want to skip them), plus an adult character role-playing as a seventeen year old.

Dean is trying to hook up with some random chick at the bar, or at least that’s what it said on the paper Dean had given them to read last night. Sam feels like it’s the punch line to a bad joke; the only people in the ‘bar’ are the three of them, because, surprise, the bunker came equipped with a 1920’s-style speak-easy, Cas is the ‘random girl,’ Dean is a demon, and Sam is pretending to be seventeen.

 

He’s not really sure what the point of this is, but what Dean wants, Dean gets, and there’s usually something good in it for the two of them anyway.

 

Sam wanders over to Dean and Cas. It’s pretty hard to be jealous of Castiel, but it’s easy to call upon years and years of memories of watching this same scene go down in bars across the lower 48 and being intensely, insanely jealous that Dean was ignoring him in favor of some girl he’d never see again.

 

Before Dean became a demon, Sam had never lusted after his brother. He’d loved Dean on a deeper level than most people could imagine. He’d been in love with Dean, and at one point, he’d wanted to spend the rest of his life with his brother. For most of his life, the love he felt for Dean was platonic or romantic, but in those awkward teenage years full of accidental touches and too-close spaces, it’d been easy for it to grow into something erotic. It never extended beyond longing glances from afar and quick, messy sessions with his right hand in the shower. He’d fallen out of love with Dean when he went to college, and back again after he rejoined the life, but the desire he’d felt for his brother for those few brief years never returned until recently.

 

For Dean, it had been slightly different. Dean had been in love with Sammy in a completely platonic way since the day their father first left them to fend for themselves in a motel room in Arkansas a few days after they’d left home. The desire hadn’t come until afterwards for him, after Sam left for college, after Sam returned.

 

Sam had always hated it though, from the time Dean starting looking at girls to the day he died, when his brother chose to whore himself out of a random chick rather than spend time with him.

 

He looks between Dean and Cas and frowns. “Deeeeean,” he whines. Castiel tries and fails to look offended at the interruption.

 

“Not now, Sammy,” Dean says, moving so that his back is towards Sam. Any other time, that tone would have had him trembling and tripping over himself to apologize.

 

“Dean, please,” he presses, putting one hand on Dean’s shoulder and pulling.

 

Castiel huffs and turns away, pretending to lose interest in Dean. Sam isn’t really sure what Cas is going to do all day, all he knows is that Dean promised him a day just for themselves. Sam sort of feels bad for Cas, because he knows the former angel gets lonely very easily, but right now he needs to focus on Dean.

 

“What is it?” Dean snaps.

 

“Dean, will you help me with my homework?” Sam asks in the whiniest tone he can manage. He’d tried to tell Dean yesterday that it didn’t make much sense for Sam to go to a bar just to ask Dean for homework help, and he’d also pointed out that Dean hadn’t been much help to him in terms of schoolwork since he was in third grade, but Dean had gotten offended and refused to change the makeshift script he’d drawn up for them to follow.

 

“Aw, Sammy, do you need your big brother to help you with your school work?”

 

Sam nods and looks down demurely, shyly clutching the edges of the school-girl skirt he’s wearing. It comes up to mid-thigh and it’s made of soft red plaid material. He’s also wearing a dark blue navy preppy sweater that Castiel, the only one of them with a functioning fashion sense, had insisted didn’t match the skirt. Dean’s eyes are drawn to the motion, and Sam gives him a small smile.

 

“Yes, big brother,” he says, slightly swaying back and forth to highlight the ruffles of the skirt.

 

Dean looks between Cas and Sam and then says, “Sorry, doll, I’ll have to catch you later,” to Cas. Then he leans in and whispers something that Sam can’t hear but that makes Castiel grin widely and giggle.

 

Sam takes Dean’s hand and leads them into the next room. It’s bare save for a chalkboard and two desks. Sam takes his place in the student’s desk while Dean shrugs off his leather jacket to reveal a smartly pressed suit and moves behind the teacher’s desk. Sam still isn’t convinced of the logic of going from one fantasy to another, but Dean had promised him that he wouldn’t regret it.

 

Dean smirks at him from the front of the room. “You’ll be taking a test today. The first part is simple. You’ll receive two points for each question you answer correctly. If you fail to answer a question on the first try, you may still receive half credit. If you fail to answer a question correctly by the second try, we’ll move on to the next one. The entire test is worth one hundred points. The various rewards for passing are listed on the board behind me.”

 

Sam takes a moment to review the rewards. If he gets a sixty-five or higher, he’ll be allowed to come. If he gets between a sixty-five and a seventy, he’ll have to make due with his own hand. If he gets between a seventy-one and an eighty, he’ll be rewarded with Dean’s own hand. If he gets between an eighty-one and a ninety, he’ll get a blowjob. And if he gets higher than a ninety, Dean will fuck him.

 

Dean’s only prepped him for the first part of the test, so he has no idea whether or not it’s brutally hard or painfully easy. Knowing Dean, it’s probably the former. He’s already hard, so he’s hoping for at least a seventy. He’s not sure what he’ll do if he fails. Dean hasn’t let him come in nearly a week, and he has the stamina of a teenager as a result.

 

“First question. What’s my name?” Dean asks with a smirk. They’ve been over this before.

 

“Mr. Winchester, sir.”

 

“Correct. What’s your name?”

 

“Sam Winchester,” Sam says before he can stop himself. Dean raises an eyebrow. “Slutty Sammy, sir,” he corrects.

 

“One point. And who do you belong to, slutty little Sammy?”

 

“You, sir,” Sam says.

 

“Good. Who’s the best big brother in the world?”

 

Sam smiles. This one is easy. “You are!”

 

“That’s right. Now, pretend you’re at a job interview. What are your goals?”

 

Sam blushes. Dean had told him what to say, but it’s still embarrassing. “To serve and to obey.”

 

“You’re doing great, Sammy. Question six. Are you male or female.”

 

“I’m a slut, sir.” Sam’s cheeks grow redder when Dean whistles.

 

“What are you wearing, slut?” Dean takes off his suit jacket and leans forward.

 

Sam spreads his legs a little, just enough that Dean can see his arousal if he tries. “A jacket and a skirt, sir.”

 

“Question eight. Are you wearing any panties?”

 

“No, sir.” Sam reaches down and hitches up his skirt a little. “See?”

 

“Nine. Why not, sweetie? Only bad girls forget to wear panties.”

 

Sam bit his lip. “I didn’t forget, sir.”

 

“Last question. Are you a bad girl, Sammy?”

 

Sam unbuttoned the top two buttons of his sweater. “The worst, sir.”

 

Dean stood up. “Nineteen points out of twenty.” He writes the score on the board. “Not bad, but it gets harder from here.”

 

Sam licks his lips. He’s only lost one point so far. “I’m a good student, sir.”

 

“You are. Now, did you prepare yourself like I told you to earlier?”

 

Sam nods. Dean had told him to stretch himself that morning, and Sam had gone all the way up to four fingers.

 

“Show me,” Dean orders.

 

Sam stands up and leans over the desk, bending over to show Dean his hole. Dean slips two fingers in right away and wiggles them around a few minutes before pulling out and wiping them and Sam’s skirt. “Nine out of ten. You’re a little loose.”

 

Sam almost whines at that. Sometimes Dean just isn’t fair. Dean writes the new score on the board, twenty-eight out of thirty. Sam’s pretty sure he’s going to pass.

 

“The next part is worth twenty-five points. You’re going to have two minutes to suck my cock. You’ll be judged on overall performance, technique, suction, and on how pretty you look on your knees.”

 

Sam gets into position kneeling before Dean. He tries to spread his legs to look as appealing as possible.

 

“Your time starts now.”

 

Sam scrambles to unzip Dean’s pants and pull his dick out of his boxers. He just barely remembers to press a tiny kiss to the head just the way Dean likes it before swallowing him down, head bobbing and cheeks hollowing as he struggles to keep up with the brutal pace he’s set for himself. His hands find Dean’s balls and gently massage them while he slurps away at Dean’s cock. He starts to hum, too, before he remembers that it’s Cas who likes that, not Dean.

 

All too soon, Dean is pulling him away and looking disappointed. Dean shakes his head, and Sam’s heart drops. “You went too fast, Sammy. You were all enthusiasm and no technique. And then you forgot who you were blowing and did that humming thing.” He clucks his tongue. “Fifteen out of twenty-five.”

 

Sam _does_ whine at that. His score is now forty-three out of fifty-five. Dean’s not going to fuck him, no matter what, and there’s no guarantee he’ll even pass now.

 

“Sorry, Sammy. You can still pass, though. The next part is worth twenty points. It’s five minutes long and all you have to do... Is be quiet.”

 

Sam closes his eyes in defeat. Dean knows every single way to make him moan, to force him to beg, to reduce him to a whimpering mess. There’s no way he’s going to do well on this part.

 

“Starting now,” Dean says, and suddenly there’s a hand on his cock. He can’t help but moan at the sensation; he wasn’t ready and he’s so achingly hard from all the pent-up frustration of the last week and from the thrill of the game they’re playing right now. Dean laughs at the sound, low and breathy against his ear, and Sam groans. Dean didn’t give him any time to steel himself, and he’s so not ready for the way Dean presses up against him or the way he’s stroking him.

 

Sam doesn’t make a noise for another minute, but then Dean presses the tip of one finger into the slit and he _wails._ Dean does it again, and again, and after the fifth time Sam gives up all pretense of being quiet and starts to moan and beg, “Please, Dean, please, oh God, please let me come.” Dean doesn’t even give him the full five minutes, just waits until he’s made twenty distinct sounds and then pulls away.

 

“I could keep going,” Dean says, “But then I’d have to start giving you negative points, and you wouldn’t have a chance.”

 

Sam is torn between being grateful and needing a hand on his dick _now._ He just nods and tries to recover as Dean writes the new score. _Forty-three out of seventy-five._ He quickly does the computation in his head. There’s no way he’s passing now. Even if he got the rest of the points, he’d only get a sixty-eight. Dean wasn’t going to touch him today, and he probably wasn’t going to come either. He’s so maddeningly hard that all he wants to do is reach down and jerk off. He’s so close he knows that it wouldn’t take very long, but that’s Dean’s decision, ultimately, so he just clenches his fists at his sides and waits for the demon to tell him what the next part of the test is.

 

“You’re going to write ‘Sammy is a slut’ on a piece of paper twenty-five times, just like it’s shown on the board. For every mistake, you’ll lose one point.”

 

Sam sighs in relief. He knows how to write; how hard could it be? Then Dean holds up a tiny vibrating plug and beckons Sam towards him. Sam whines, but rises and presents to Dean nonetheless. Dean slips the plug in, twists it, then pulls it out several times before slapping Sam’s ass and telling him to sit down.

 

Dean throws him a pen and Sam catches it expertly. He manages to write one sentence before Dean turns on the vibrator. He jolts and the pen goes scribbling across the page. He winces, but forces himself to go on. It’s only one mistake.

 

He goes as slowly as he dares. The plug is pressed _right_ against his prostate, sending little jolts of pleasure through him with each vibration. Dean’s trying his best to be unpredictable, turning it on and off and up and down randomly, but Sam is on his fifteenth one and hasn’t made another mistake yet. Then Dean turns it all the way up and he skips an ‘m’ in Sammy. He knows that Dean’s already seen it, so he moves on reluctantly.

 

By the time he’s done with the second to last one, he can barely concentrate. He’s desperate to come, rocking back and forth and trying to push the plug deeper. He accidently forgets to capitalize the last sentence. He sees it just when he’s putting in the last period. “Done,” he gasps, throwing the pen down and pushing the paper towards Dean. The vibrator goes off and he moans in disappointment. He’s happy, though. He’s only made three mistakes. He’ll get a sixty-five, and Dean will let him reach down and-

 

“Oh, Sammy.” Dean sounds strangely disappointed, but Sam is just confused. He only made three mistakes, he’s passed, he came come, can’t he? “Baby, you only did twenty-four,” Dean says as he hands the paper back to Sam.

 

Sam rips it from Dean and counts. Twenty-two, twenty-three, twenty-four... Twenty-four. Sam feels a sob well up in his chest and pushes it down savagely. “But I was so close,” he whines. “I was so-so-so-so close and... Please, Master, please, I need to come, please, please, _please_ let me!” He rises from his chair and falls to his knees in front of Dean. “Please,” he sobs.

 

Dean pets his hair for a while before speaking. “Up,” he says. Sam stands, and keens at the loss when Dean pulls the vibrator out and drops it on the desk. “Come on, Sammy, I’ll get you a snack while you calm down and then we can go out somewhere, just you and me. Okay?”

 

Sam nods, unable to think past the steady thrum of _want-need-want_ pulsing through his veins.

 

“It’s okay, baby. You’re okay,” Dean soothes, and slowly Sam sinks back into his favorite role: that of Dean’s loving, loyal, obedient pet.

**Author's Note:**

> Prompts + requests are welcome.


End file.
